Alkylbenzyltriphenylphosphonium chlorides



2,946,824 ALKYLBENZXLIRIPHENYLPHQ-SBHONIUM CHLO Argyl, Pa, assignors to-Gen'eralf 8i 1 ilnfCfr-v poration, New York, N.Y., acprpor'a 'qn' of'Delaware N Dran n- Filed ion-.15.,-nssi'sa-ng. 61.294

' was; (or; not 06:5)

The present invention relates tea-new classoflquatennary compounds having new and valuable industrial; and agricultural uses. class of alkylbenzyltriphenylphosphonium chlorides;

We have found that a new classof quaternary corn--- are readily p p y q ir s nsv 'm .1e ..Qf 1-a. i a kylated benzyl chloride with 1 mole ofi t-niphenylphosvent diluent and at a temperature ranging from 145- United States.

154, talline solids which are water soluble:

It relates 2 Particularly to a newg A 160 C. for-a, period; of. timearanging from. 2 to, 4hours. A

As e amples of of. and. pralkylated heuzyl: ch10- rides that may be; condensed w' -h triphenylphosphine, the followingare illustrative: 7 1

Octylbenzyhch-loride Nonylbenzyl chloride Decylbenzyl: chloride Hend'ecylbenzyl; chloride Dodecylbenzyl chloride Cetylbenzyl chloride Octadecylbenzyl chloride The following examples will illustrate the manner in which the alkylbenzyltriphenylphosphonium chlorides are prepared and utilized as valuable agricultural chemicals having new and unexpected properties.

EXAMPLE'I Into a 500 ml. flask equipped with a stirrer, therphine in the presence of chlorobenzene as arr-inert sol-- --Alkylbenzylmghenylghosghomum chip-nae;

Example If was again repeatedwith theiexceptionl that the: charge; of? coreactantsl consisted of 7826;. grams of trip'henylphos'phine,;. 113.4 grams. of. m octadpcylhenzyl chloride and 100 grams of monochlorbenzene; The

charge was heated-,to refltmfor 3 ,hours at 150 C;-

After cooling,'filtering and washing with petroleum ether followed by drying; the white crystalline. solid fis soluble irr'watep; w By following-the-procedure onnxample I,

of dodecylbenzyl chloride wererepl aced by an equivalent amount of p-nonylbenzyl chloride, p-decylbenzyl chloride, 'prhendecylbenzyl chloride and m-cetylbenzyl h de r rli e n to. y d the ll winawhit ,srr

: p-Nonylhenzyltriphenylpliosphonium "chloride p-Decylbenzyltriphenylphosphonium chloride p-Hendecylbenzyltriphenyl phosphonium chloride ni-Cetylbenzyltriphenylphosplroniunr chloride 7 In order to determine'whethen the foregoing alltyl benzyltriphenylphosphn illmhalides were. efii'ciqnt'i s, inrsecticides, thefollowing test, procedurev was; reontedjtoz 1 rain the; following ingredients:

C nq t m th ff alky h nzr in'in s r rh .phgniu halides, of the; foregoing examples weremade-to congrams Acetone q m I 10 Water. soluble surface, active agent" ml 0.02 Water suflicient to make "m ll.-. .100

3 all of the following screening tests:

mometer and condenser were placed 78.6 grams (0.3

mole) of triphenylphosphine, 88.3 grams (0.3 mole) of p-dodecylbenzyl chloride and 83.5 grams of monochlorbenzene. The charge was heated to reflux at 150l57 C. and held at this temperature for a total-of 2% hours. The contents of the flask were then cooled and dissolved in 450 ml. of carbon tetrachloride with gentle Warming. The reaction mixture was then cooled (5f C.) in an ice bath and filtered. The white crystalline Test insect ing method. The test larvae are removed from the colony and held without food, in a glass dish, for 4 hours prior to being placed on the treated foliage.

Application of 'toxicant Paired seed leaves, excised from tender green bean' plants, are dipped in the test formulations'until they are thoroughly wetted. Excess liquid is removed by gentle shaking. While the leaves are drying in a ventilated 7 hood, wilting is prevented by placing the stem in water.

solid after Washing with a commercially available high boiling petroleum ether was dried in an" oven at 100 C. The resulting dodecylbenzyltriphenylphosphoniurn chloride is soluble in water.

EXAMPLE 11 When dry, the paired leaves are separated and each is placed in a 9 cm. Petri dish lined with. filter paper. Ten randomly'selected larvae are introduced before closing the dish.

Holding conditions The closed dishes are labeled and held at to F. for 3 days. Although the larvae can easily consume the whole leaf within 24 hours no more food is a r lc .Bat'elstefl July 26,1960

action.

Record of results Larvae which are unable to move the length of the" Concentration of toxicant test compounds are formulated by a standard procedure of solution in acetone, addition of an emulsifier (surfactant) and dilution with water. Primary screenpending upon the strength the composition, preferably from .01 to 20%.

We claim: 1. Alkylbenzyltriphenylphosphonium chlorides having 5 the following general formula:

wherein R represents an alkyl group containing from 8 to 18 carbon atoms. r e 2. p-dodecylbenzyltriphenylphosphonium chloride. 3. p-octylbenzyltriphenylphosphonium chloride.

ing tests are run at 2000 p.p.m. 4. m-octadecylbenzyltriphenylphosphonium chloride.

Results of tests Percent Alkylbenzyltriphenylphosphonium Chloride p.p.m. Living Dead Percent Rating Feeding Control Inhibition dodecylbenzyltriphenylphosphonium chloride- 2, 000 2 8 80 95 octylbenzyltriphenylphosphonium chloride 2, 000 2 8 80 95 octyldecylbenzyltriphenylphosphonuim chloride 2,000 2 8 80 95 nonylbenzyltriphcnylphosphonium chloride-. 2,000 2 8 80 95 decylbenzyltriphenylphosphonimn chloride-.- 2, 000 2 8 80 95 hendecylbenzyltriphenylphosphonium chloride 7 2,000 2 8 V '80 95 cetylbenzyltriphenylphosphoniurn chloride... 2,000 2 8 80 95 Lindane 350 1 9 90 Very good...-- 97 Blank Control 10 0 0 benzyltriphenylphosphonium chloride 2, 000 6 3 Unprornising. 10

Solvents which may be employed in preparing insec- 5. p-decylbenzyltriphenylphosphonium chloride.

ticidal solutions are water, refined petroleum distillates, 6. m-cetylbenzyltriphenylphosphonium chloride.

' liquid halogenated hydrocarbon compounds, such as carbon tetrachloride, chloroform, ethylene chloride, chlorobenzene, hydrocarbon compounds, such as benzene and toluene; lower aliphatic alcohols, such as methyl, ethyl or propyl alcohol.

Solid inert carriers, such as tentom'te, diatomaceous earth, wood flour, etc. may also be employed for use in dusting powders. The quantity of carrier whether liquid or solid can be varied between Wide limits de- Kosolapoff: Organophosphorus Compounds, John Wiley & Sons, Inc., New York (1950), page 90.

Wertheim: Textbook of Organic Chemistry, 3rd edition, McGraw-Hill pages 6-8.

Book Co., Inc., New York (1951), 

1. ALKYLBENZYLTRIPHENYLPHOSPHONIUM CHLORIDES HAVING THE FOLLOWING GENERAL FORMULA: 